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Diversification of Naphthol Skeletons Triggered by Aminative Dearomatization

Linqiang Li, Dong Wang, Yue Zhang, Jingjing Liu, Han Wang*, Xinjun Luan*

*College of Chemistry & Materials Science, Northwest University, Xi’an 710127, China, Email: hanwangnwu.edu.cn, xluannwu.edu.cn

L. Li, D. Wang, Y. Zhang, J. Liu, H. Wang. X. Luan, Org. Lett., 2024, 26, 4910-4915.

DOI: 10.1021/acs.orglett.4c01416


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Abstract

A silver-catalyzed aminative dearomatization of naphthols enables skeletal diversifications including ring expansion, ring opening, ring contraction, and atom transmutation to provide a diverse array of azepinones, unsaturated amides, isoquinolines, and indenones. Mechanistic investigations suggest the intermediacy of the dearomatized intermediates. ​

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The document discusses a silver-catalyzed aminative dearomatization of naphthols, which has been developed to enable various skeletal diversifications such as ring expansion, ring opening, ring contraction, and atom transmutation. This method allows the synthesis of diverse compounds like azepinones, unsaturated amides, isoquinolines, and indenones from naphthol substrates. The approach is significant for its potential applications in synthesizing bioactive and functional molecules, as well as converting complex molecular skeletons. Mechanistic studies indicate that dearomatized intermediates play a crucial role in these transformations. The process involves treating 1-phenyl-2-naphthol with PhI=NTs, Cs2CO3, and MgO, yielding products in high efficiency. The study also explores the substrate scope, showing good yields for various substituted naphthols. Additionally, the document highlights the integration of nitrogen insertion and acidic hydrolysis for ring-opening protocols and the use of FeCl3 for ring contraction. The research underscores the potential of skeletal editing as a robust strategy in organic synthesis, offering a pathway to achieve target compounds without de novo synthesis. The findings open avenues for preparing a broader range of molecular skeletons through combinations with other synthetic transformations.


Key Words

benzo-fused N-heterocycles


ID: J54-Y2024